CN101573324B - 芳胺化合物和电子器件 - Google Patents
芳胺化合物和电子器件 Download PDFInfo
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- CN101573324B CN101573324B CN2006800568600A CN200680056860A CN101573324B CN 101573324 B CN101573324 B CN 101573324B CN 2006800568600 A CN2006800568600 A CN 2006800568600A CN 200680056860 A CN200680056860 A CN 200680056860A CN 101573324 B CN101573324 B CN 101573324B
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- phenyl
- compound
- negative electrode
- phenylbenzene
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- -1 Arylamine compounds Chemical class 0.000 title claims abstract description 55
- 150000001875 compounds Chemical class 0.000 claims abstract description 107
- 239000000203 mixture Substances 0.000 claims description 48
- 229910052757 nitrogen Inorganic materials 0.000 claims description 44
- 239000000463 material Substances 0.000 claims description 40
- 230000005540 biological transmission Effects 0.000 claims description 38
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 claims description 30
- 239000000243 solution Substances 0.000 claims description 28
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 26
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 23
- 238000002347 injection Methods 0.000 claims description 20
- 239000007924 injection Substances 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical class C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 16
- 230000000903 blocking effect Effects 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 239000011575 calcium Substances 0.000 claims description 12
- 238000000576 coating method Methods 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 239000004411 aluminium Substances 0.000 claims description 8
- 229910052782 aluminium Inorganic materials 0.000 claims description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 8
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 claims description 7
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 6
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 6
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 claims description 6
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 claims description 6
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 claims description 6
- 125000005561 phenanthryl group Chemical group 0.000 claims description 6
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 claims description 6
- 125000001725 pyrenyl group Chemical group 0.000 claims description 6
- 238000004528 spin coating Methods 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- LJJQENSFXLXPIV-UHFFFAOYSA-N fluorenylidene Chemical group C1=CC=C2[C]C3=CC=CC=C3C2=C1 LJJQENSFXLXPIV-UHFFFAOYSA-N 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
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- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 claims description 4
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- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 4
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- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 4
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- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
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- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 claims description 3
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- DIOURSRLPLXSNY-UHFFFAOYSA-N 2-[3,5-bis(4-phenyl-1h-benzimidazol-2-yl)phenyl]-4-phenyl-1h-benzimidazole Chemical compound C1=CC=CC=C1C1=CC=CC2=C1NC(C=1C=C(C=C(C=1)C=1NC3=C(C=4C=CC=CC=4)C=CC=C3N=1)C=1NC3=C(C=4C=CC=CC=4)C=CC=C3N=1)=N2 DIOURSRLPLXSNY-UHFFFAOYSA-N 0.000 claims description 2
- 229910001148 Al-Li alloy Inorganic materials 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
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- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 2
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- OEZQCMMAFSEXQW-UHFFFAOYSA-N calcium silver Chemical compound [Ca].[Ag] OEZQCMMAFSEXQW-UHFFFAOYSA-N 0.000 claims description 2
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- 229910052738 indium Inorganic materials 0.000 claims description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims description 2
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- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 claims description 2
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- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 2
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- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims description 2
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- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 2
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- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 claims 3
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- Engineering & Computer Science (AREA)
- Optics & Photonics (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electromagnetism (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
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PCT/SG2006/000383 WO2008069756A1 (en) | 2006-12-08 | 2006-12-08 | Arylamine compounds and electronic devices |
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CN101573324A CN101573324A (zh) | 2009-11-04 |
CN101573324B true CN101573324B (zh) | 2013-11-20 |
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US (1) | US8518559B2 (ja) |
EP (1) | EP2121573A4 (ja) |
JP (1) | JP5121848B2 (ja) |
KR (1) | KR101434632B1 (ja) |
CN (1) | CN101573324B (ja) |
TW (1) | TWI435861B (ja) |
WO (1) | WO2008069756A1 (ja) |
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KR102340209B1 (ko) | 2007-12-03 | 2021-12-17 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 카바졸 유도체, 및 카바졸 유도체를 사용하는 발광 소자, 발광 장치 및 전자 기기 |
EP2415752B1 (en) * | 2009-03-19 | 2016-03-09 | Idemitsu Kosan Co., Ltd. | Aromatic amine derivative and organic electroluminescent element using same |
JP5617202B2 (ja) * | 2009-07-24 | 2014-11-05 | 三菱化学株式会社 | 有機化合物、電荷輸送材料、有機電界発光素子用組成物、有機電界発光素子、有機elディスプレイ及び有機el照明 |
WO2011021520A1 (ja) | 2009-08-19 | 2011-02-24 | 出光興産株式会社 | 芳香族アミン誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
US8455042B2 (en) | 2009-11-17 | 2013-06-04 | General Electric Company | Method for making material useful in optoelectronic device, the material and the optoelectronic device |
JP5623996B2 (ja) | 2010-09-21 | 2014-11-12 | 株式会社半導体エネルギー研究所 | カルバゾール誘導体 |
JP5872861B2 (ja) | 2010-11-30 | 2016-03-01 | 株式会社半導体エネルギー研究所 | カルバゾール化合物 |
US9269908B2 (en) * | 2011-04-21 | 2016-02-23 | Nano And Advanced Materials Institute Limited | Bipolar compound as a host material for organic light emitting diodes |
KR20130009619A (ko) * | 2011-07-06 | 2013-01-23 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 발광 소자, 발광 장치, 표시 장치, 조명 장치 및 전자 기기 |
KR101701246B1 (ko) * | 2011-08-05 | 2017-02-03 | 삼성디스플레이 주식회사 | 카바졸계 화합물 및 이를 포함한 유기 발광 소자 |
KR20190000390A (ko) | 2012-08-03 | 2019-01-02 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 발광 소자, 발광 장치, 전자 장치 및 조명 장치 |
CN104269493B (zh) * | 2014-10-13 | 2017-02-01 | 山东大学 | 一种有机单晶自旋二极管及其制备方法 |
CN104409645B (zh) * | 2014-11-07 | 2017-05-24 | 南京邮电大学 | 一种暖白光oled器件及其制备方法 |
JP6613561B2 (ja) * | 2014-12-12 | 2019-12-04 | 日立化成株式会社 | 有機エレクトロニクス材料及び有機エレクトロニクス素子 |
KR101688222B1 (ko) * | 2015-06-29 | 2016-12-22 | 한국기계연구원 | 태양전지용 정공수송층 조성물, 이의 제조방법 및 이를 포함하는 태양전지 |
EP3257849A1 (en) * | 2016-06-14 | 2017-12-20 | Solvay SA | Organic semiconductor composition and semiconducting layer obtained therefrom |
EP3305766A4 (en) | 2016-06-28 | 2018-06-13 | Duk San Neolux Co., Ltd. | Compound for organic electrical element, organic electrical element using same, and electronic device therefor |
KR102192216B1 (ko) | 2017-12-26 | 2020-12-16 | 주식회사 엘지화학 | 아민계 화합물 및 이를 포함하는 유기 발광 소자 |
KR102275231B1 (ko) * | 2018-05-11 | 2021-07-08 | 주식회사 엘지화학 | 함질소 고리 화합물 및 이를 포함하는 색변환 필름 |
CN110105333A (zh) * | 2019-04-29 | 2019-08-09 | 武汉华星光电半导体显示技术有限公司 | 电致发光材料、电致发光材料的制备方法及发光器件 |
CN110105264A (zh) * | 2019-04-29 | 2019-08-09 | 武汉华星光电半导体显示技术有限公司 | 电致发光材料、电致发光材料的制备方法及发光器件 |
CN110483529B (zh) * | 2019-08-09 | 2021-04-13 | 宁波卢米蓝新材料有限公司 | 一种稠杂环化合物及其应用 |
TWI826984B (zh) * | 2021-05-07 | 2023-12-21 | 大立碳易股份有限公司 | 導電高分子材料的用途 |
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- 2006-12-08 CN CN2006800568600A patent/CN101573324B/zh active Active
- 2006-12-08 US US12/518,089 patent/US8518559B2/en not_active Expired - Fee Related
- 2006-12-08 WO PCT/SG2006/000383 patent/WO2008069756A1/en active Application Filing
- 2006-12-08 EP EP06824654A patent/EP2121573A4/en not_active Withdrawn
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Also Published As
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EP2121573A1 (en) | 2009-11-25 |
EP2121573A4 (en) | 2010-08-11 |
TWI435861B (zh) | 2014-05-01 |
WO2008069756A8 (en) | 2008-08-28 |
KR20090097862A (ko) | 2009-09-16 |
US20100133519A1 (en) | 2010-06-03 |
KR101434632B1 (ko) | 2014-08-27 |
JP5121848B2 (ja) | 2013-01-16 |
US8518559B2 (en) | 2013-08-27 |
WO2008069756A1 (en) | 2008-06-12 |
JP2010511700A (ja) | 2010-04-15 |
TW200837037A (en) | 2008-09-16 |
CN101573324A (zh) | 2009-11-04 |
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